I had this problem when the cold weather started coming in. I know that temperature can cause the psi to drop below the recommended pressure, so you have to add air. My local dealership has nitrogen gas (I think that's what it is) that they can fill your tires with so that you don't have to worry about temperature changes. The nitrogen doesn't expand or contract with cooler temps. If this is not your problem, sounds like you have a leek if it's the same tire you're filling up.